A chameleon catalyst for nonheme iron-promoted olefin oxidation

Shyam R. Iyer; Maedeh Moshref Javadi; Yan Feng; Min Young Hyun; Williamson N. Oloo; Cheal Kim; Lawrence Que

doi:10.1039/c4cc06164k

A chameleon catalyst for nonheme iron-promoted olefin oxidation

Shyam R. Iyer, Maedeh Moshref Javadi, Yan Feng, Min Young Hyun, Williamson N. Oloo, Cheal Kim, Lawrence Que

Chemistry (Twin Cities)

Research output: Contribution to journal › Article › peer-review

27 Scopus citations

Abstract

We report the chameleonic reactivity of two nonheme iron catalysts for olefin oxidation with H₂O₂ that switch from nearly exclusive cis-dihydroxylation of electron-poor olefins to the exclusive epoxidation of electron-rich olefins upon addition of acetic acid. This switching suggests a common precursor to the nucleophilic oxidant proposed to Fe^III-ζ²-OOH and electrophilic oxidant proposed to Fe^V(O)(OAc), and reversible coordination of acetic acid as a switching pathway.

Original language	English (US)
Pages (from-to)	13777-13780
Number of pages	4
Journal	Chemical Communications
Volume	50
Issue number	89
DOIs	https://doi.org/10.1039/c4cc06164k
State	Published - Oct 14 2014

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title = "A chameleon catalyst for nonheme iron-promoted olefin oxidation",

abstract = "We report the chameleonic reactivity of two nonheme iron catalysts for olefin oxidation with H2O2 that switch from nearly exclusive cis-dihydroxylation of electron-poor olefins to the exclusive epoxidation of electron-rich olefins upon addition of acetic acid. This switching suggests a common precursor to the nucleophilic oxidant proposed to FeIII-ζ2-OOH and electrophilic oxidant proposed to FeV(O)(OAc), and reversible coordination of acetic acid as a switching pathway.",

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AU - Iyer, Shyam R.

AU - Javadi, Maedeh Moshref

AU - Feng, Yan

AU - Hyun, Min Young

AU - Oloo, Williamson N.

AU - Kim, Cheal

AU - Que, Lawrence

PY - 2014/10/14

Y1 - 2014/10/14

N2 - We report the chameleonic reactivity of two nonheme iron catalysts for olefin oxidation with H2O2 that switch from nearly exclusive cis-dihydroxylation of electron-poor olefins to the exclusive epoxidation of electron-rich olefins upon addition of acetic acid. This switching suggests a common precursor to the nucleophilic oxidant proposed to FeIII-ζ2-OOH and electrophilic oxidant proposed to FeV(O)(OAc), and reversible coordination of acetic acid as a switching pathway.

AB - We report the chameleonic reactivity of two nonheme iron catalysts for olefin oxidation with H2O2 that switch from nearly exclusive cis-dihydroxylation of electron-poor olefins to the exclusive epoxidation of electron-rich olefins upon addition of acetic acid. This switching suggests a common precursor to the nucleophilic oxidant proposed to FeIII-ζ2-OOH and electrophilic oxidant proposed to FeV(O)(OAc), and reversible coordination of acetic acid as a switching pathway.

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VL - 50

SP - 13777

EP - 13780

JO - Chemical Communications

JF - Chemical Communications

IS - 89

ER -

A chameleon catalyst for nonheme iron-promoted olefin oxidation

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